Naphthalocyanine derivatives and their use in optical recording medium

Abstract

Novel naphthalocyanine derivatives are disclosed in the specification are useful for forming a recording layer in an optical recording medium. These derivatives are represented by the following formula (I): ##STR1## in which k, l, m and n, which may be the same or different, are zero or integers of 1 to 4, k+l+m+n being an integer of 1 or more; R 1 's in a number of (k+l+m+n), which may be the same or different, are alkyl groups, substituted alkyl groups, or aryl groups; M is Si, Ge or Sn; and two Y's, which may be the same or different, are aryloxyl groups, alkoxyl groups, trialkylsiloxyl groups, triarylsiloxyl groups, trialkoxysiloxyl groups, triaryloxysiloxyl groups, trityloxyl groups, or acyloxyl groups. These derivatives are especially useful in the preparation of an optical recording medium.

What is claimed is: 
     
       1. A naphthalocyanine derivative represented by the formula: ##STR32## wherein k, l, m and n, which may be the same or different, are zero or integers of 1 to 4, k+l+m+n being an integer of 1 or more; R 1  's in a number of 4(k+l+m+n), which may be the same or different, are alkyl groups, substituted alkyl groups, or aryl groups; M is Si, Ge or Sn; and two Y's, which may be the same or different, are aryloxyl groups, alkoxyl groups, trialkylsiloxyl groups, triarylsiloxyl groups, trialkoxysiloxyl groups, triaryloxysiloxyl groups, trityloxyl groups, or acyloxyl groups. 
     
     
       2. A naphthalocyanine derivative according to claim 1, wherein M is Si or Ge in the formula (I). 
     
     
       3. A naphthalocyanine derivative according to claim 1, wherein k, l, m and n are all 1 in the formula (I). 
     
     
       4. A naphthalocyanine derivative according to claim 1, wherein two Y's are trialkylsiloxyl groups in the formula (I). 
     
     
       5. A naphthalocyanine derivative according to claim 1, wherein all R 1  's are alkyl groups having 1 to 22 carbon atoms in the formula (I). 
     
     
       6. A naphthalocyanine derivative according to claim 1, wherein all R 1  's are substituted alkyl groups in the formula (I). 
     
     
       7. A naphthalocyanine derivative according to claim 1, wherein the aryloxyl groups are selected from the group consisting of phenoxyl group, tolyloxyl group and anisyloxyl group; the alkoxyl groups are selected from the group consisting of amyloxyl group, hexyloxyl group, octyloxyl group, decyloxyl group, dodecyloxyl group, tetradecyloxyl group, hexadecyloxyl group, octadecyloxyl group, eicosyloxyl group and docosyloxyl group; the trialkylsiloxyl groups are selected from the group consisting of trimethylsiloxyl group, triethylsiloxyl group, tripropylsiloxyl group and tributylsiloxyl group; the triarylsiloxyl groups are selected from the group consisting of triphenylsiloxyl group, trianisylsiloxyl group and tritolylsiloxyl group; the trialkoxysiloxyl groups are selected from the group consisting of trimethoxysiloxyl group, triethoxysiloxyl group, tripropoxysiloxyl group and tributoxysiloxyl group; the triaryloxysiloxyl groups are selected from the group consisting of triphenoxysiloxyl group, trianisiloxysiloxyl group and tritolyloxysiloxyl group; and the acyloxyl groups are selected from the group consisting of acetyoxyl group, propionyloxyl group, butyryloxyl group, valeryloxyl group, pivaloyloxyl group, hexanoyloxyl group and octanoyloxyl group. 
     
     
       8. A naphthalocyanine derivative according to claim 5, wherein the aryloxyl groups are selected from the group consisting of phenoxyl group, tolyloxyl group and anisyloxyl group; the alkoxyl groups are selected from the group consisting of amyloxyl group, hexyloxyl group, octyloxyl group, decyloxyl group, dodecyloxyl group, tetradecyloxyl group, hexadecyloxyl group, octadecyloxyl group, eicosyloxyl group and docosyloxyl group; the trialkylsiloxyl groups are selected from the group consisting of trimethylsiloxyl group, triethylsiloxyl group, tripropylsiloxyl group and tributylsiloxyl group; the triarylsiloxyl groups are selected from the group consisting of triphenylsiloxyl group, trianisylsiloxyl group and tritolylsiloxyl group; the trialkoxysiloxyl groups are selected from the group consisting of trimethoxysiloxyl group, triethoxysiloxyl group, tripropoxysiloxyl group and tributoxysiloxyl group; the triaryloxysiloxyl groups are selected from the group consisting of triphenoxysiloxyl group, trianisiloxysiloxyl group and tritolyloxysiloxyl group; and the acyloxyl groups are selected from the group consisting of acetyoxyl group, propionyloxyl group, butyryloxyl group, valeryloxyl group, pivaloyloxyl group, hexanoyloxyl group and octanoyloxyl group. 
     
     
       9. A naphthalocyanine derivative according to claim 1, wherein Y in the formula (I) is a trialkoxysiloxyl group, a triaryloxysiloxyl group, a trityloxyl group or an acyloxyl group. 
     
     
       10. A naphthalocyanine derivative according to claim 1, wherein Y in the formula (I) is a trialkoxysiloxyl group. 
     
     
       11. A naphthalocyanine derivative according to claim 1, wherein Y in the formula (I) is a trialkoxysiloxyl group, a triaryloxysiloxyl group, a trityloxyl group or an acyloxyl group; and R 1  is an alkyl group. 
     
     
       12. A naphthalocyanine derivative according to claim 1, wherein Y in the formula (I) is a trialkoxysiloxyl group; and R 1  is an alkyl group. 
     
     
       13. An optical recording medium comprising a substrate and a recording layer formed on a surface of the substrate, said recording layer comprising mainly a naphthalocyanine derivative represented by the formula: ##STR33## wherein k, l, m and n, which may be the same or different, are zero or integers of 1 to 4, k+l+m+n being an integer of 1 or more; R 1  's in a number of 4 (k+l+m+n), which may be the same or different, are alkyl groups, substituted alkyl groups, or aryl groups; M is Si, Ge or Sn; and two Y's, which may be the same or different, are aryloxyl groups, alkoxyl groups, trialkylsiloxyl groups, triarylsiloxyl groups, trialkoxysiloxyl groups, triaryloxysiloxyl groups, trityloxyl groups, or acyloxyl groups. 
     
     
       14. An optical recording medium according to claim 13, wherein the recording layer comprises mainly a naphthalocyanine derivative of the formula (I) in which M is Si or Ge. 
     
     
       15. An optical recording medium according to claim 13, wherein the recording layer is composed mainly of a naphthalocyanine derivative of the formula (I) in which k, l, m and n are all 1. 
     
     
       16. An optical recording medium according to claim 13, wherein the recording layer is composed mainly of a naphthalocyanine derivative of the formula (I) in which two Y's are trialkylsiloxyl groups. 
     
     
       17. An optical recording medium according to claim 13, wherein the recording layer is composed mainly of a naphthalocyanine derivative of the formula (I) in which all R 1  's are alkyl groups having 1 to 22 alkyl groups. 
     
     
       18. An optical recording medium according to claim 13, wherein the recording layer is composed mainly of a naphthalocyanine derivative of the formula (I) in which all R 1  's are substituted alkyl groups. 
     
     
       19. An optical recording medium according to claim 13, wherein the aryloxyl groups are selected from the group consisting of phenoxyl group, tolyloxyl group and anisyloxyl group; the alkoxyl groups are selected from the group consisting of amyloxyl group, hexyloxyl group, octyloxyl group, decyloxyl group, dodecyloxyl group, tetradecyloxyl group, hexadecyloxyl group, octadecyloxyl group, eicosyloxyl group and docosyloxyl group; the trialkylsiloxyl groups are selected from the group consisting of trimethylsiloxyl group, triethylsiloxyl group, tripropylsiloxyl group and tributylsiloxyl group; the triarylsiloxyl groups are selected from the group consisting of triphenylsiloxyl group, trianisylsiloxyl group and tritolylsiloxyl group; the trialkoxysiloxyl groups are selected from the group consisting of trimethoxysiloxyl group, triethoxysiloxyl group, tripropoxysiloxyl group and tributoxysiloxyl group; the triaryloxysiloxyl groups are selected from the group consisting of triphenoxysiloxyl group, trianisiloxysiloxyl group and tritolyloxysiloxyl group; and the acyloxyl groups are selected from the group consisting of acetyoxyl group, propionyloxyl group, butyryloxyl group, valeryloxyl group, pivaloyloxyl group, hexanoyloxyl group and octanoyloxyl group. 
     
     
       20. An optical recording medium according to claim 17, wherein the aryloxyl groups are selected from the group consisting of phenoxyl group, tolyloxyl group and anisyloxyl group; the alkoxyl groups are selected from the group consisting of amyloxyl group, hexyloxyl group, octyloxyl group, decyloxyl group, dodecyloxyl group, tetradecyloxyl group, hexadecyloxyl group, octadecyloxyl group, eicosyloxyl group and docosyloxyl group; the trialkylsiloxyl groups are selected from the group consisting of trimethylsiloxyl group, triethylsiloxyl group, tripropylsiloxyl group and tributylsiloxyl group; the triarylsiloxyl groups are selected from the group consisting of triphenylsiloxyl group, trianisylsiloxyl group and tritolylsiloxyl group; the trialkoxysiloxyl groups are selected from the group consisting of trimethoxysiloxyl group, triethoxysiloxyl group, tripropoxysiloxyl group and tributoxysiloxyl group; the triaryloxysiloxyl groups are selected from the group consisting of triphenoxysiloxyl group, trianisiloxysiloxyl group and tritolyloxysiloxyl group; and the acyloxyl groups are selected from the group consisting of acetyoxyl group, propionyloxyl group, butyryloxyl group, valeryloxyl group, pivaloyloxyl group, hexanoyloxyl group and octanoyloxyl group.